V. K. Gavrilov, I. V. Chuchelkin, S. V. Zheglov, I. D. Firsin, A. A. Shiryaev, K. N. Gavrilov, A. V. Maximychev, A. M. Perepukhov, N. S. Goulioukina, I. P. Beletskaya, “Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis”, Mendeleev Commun., 2019, Volume 29, Issue 1,Pages 35

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Communications

Chiral inducers with (1R,2R)-1,2-diaminocyclohexane core for organo- and metallocatalysis

V. K. Gavrilov^a, I. V. Chuchelkin^a, S. V. Zheglov^a, I. D. Firsin^a, A. A. Shiryaev^a, K. N. Gavrilov^a, A. V. Maximychev^b, A. M. Perepukhov^b, N. S. Goulioukina^cd, I. P. Beletskaya^cd

^a Department of Chemistry, S.A. Esenin Ryazan State University, Ryazan, Russian Federation
^b Moscow Institute of Physics and Technology (National Research University), Dolgoprudny, Moscow Region, Russian Federation
^c A.N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Moscow, Russian Federation
^d Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation

Abstract: A P*-chiral diamidophosphite ligand of the 1,3,2-diazaphospholidine series was obtained by direct phosphorylation of N-[(1R,2R)-2-(tert-butoxycarbonylaminocyclohexyl)]-N′-[(1R)-1-(hydroxymethyl)propyl]oxalamide. The use of this ligand made it possible to reach 98% ee in the Pd-catalyzed allylation involving (E)-1,3-diphenylallyl acetate, 81% ee in the allylation of ethyl 2-oxocyclohexane-1-carboxylate with cinnamyl acetate, 78% ee in the Rh-catalyzed hydrogenation of methyl (Z)-2-acetamido-3-phenylacrylate, and 32% ee in the Rh- and Ir-catalyzed hydrosilylation of (E)-N-(4-methoxyphenyl)-1-phenylethan-1-imine with diphenylsilane. The above mentioned oxalamide provides up to 50% ee in the organocatalytic reduction of the same imine.

Language: English

DOI: 10.1016/j.mencom.2019.01.010

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